Together with Krahulik, Holkins created the Penny Arcade Expo beginning in 2004, a series of gaming festivals held in Seattle, Boston, Australia,[1] and San Antonio. He is also a co-founder of Child's Play, a multimillion dollar charity which organizes toy drives for children's hospitals.

Along with Krahulik, Holkins was included on the 2010 Time 100[2] for their work on Penny Arcade.

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Holkins and Krahulik had the opportunity to play the new release of Dungeons & Dragons Fourth Edition in Seattle for a day with Chris Perkins from Wizards of the Coast, Scott Kurtz of PvP, and Wil Wheaton.[3] Jerry is also featured in the Dungeons and Dragons 4E podcast, playing a character named Omin Dran, a Cleric of the Goddess Avandra, and CEO of an adventuring party named Acquisitions Incorporated.

Outside of Penny Arcade and Child's Play, Holkins also sings and plays guitar in the band The Fine Print, whose music can be downloaded for free. In the past, the Fine Print has opened for the band Anal Cunt.[4]

Along with being the co-creator and writer for the Penny Arcade webcomic, Holkins is also the basis for one of the two central characters, "Tycho Brahe", sharing similar interests and personalities;[5] though their appearances differ (for example, Tycho has mussed hair and sideburns, while Holkins's head is shaven).[6][7] Holkins, along with Krahulik, posts written updates accompanying each comic. These posts are often computer and video game commentary, but also include personal reflections or rants. The two have been said to provide a representation of the diversity of styles among gamers, with Krahulik representing action-oriented gamers and Holkins representing the more cerebral players.[8] It has been mutually agreed between Krahulik and Holkins that Penny Arcade would not be the same with just one of them.

"Epic Legends of the Hierarchs: The Elemenstor Saga"[9] (abbreviated as ELotH:TES) is a fan-driven parody of the generic fantasy fiction that serves as the backstory of many fantasy game franchises. It was created by Holkins as a single PBWiki page and rapidly grew in size as Penny Arcade fans joined in expanding the parody.

The tales of the Saga itself rotate around several (non-existent) bases: The original 13 'canon' books, the Japanese anime series, the American re-make of the anime, the collectible card game, and even the odd life of the author himself, and such events as his several-year long "drinking and pill binge." These are only the major pieces of the story, and other fragments abound. A version of the wiki is available for purchase in the form of a reference guide to the 13 novel series.